(a) Field of the Invention
The invention relates to substituted N-cycloalkylmethyl-1H-pyrazolo[3,4-b]quinolin-4-amines, to pharmaceutical compositions containing them and to methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them.
(b) Information Disclosure Statement
Crenshaw et al., J. Med. Chem. 1976, 19 (2), 262-275, disclose a series of N-substituted-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolin-4-amines which are said to be useful as interferon inducing agents. Specifically disclosed are N-cyclopropyl, N-tricyclo[3.3.1.13,7]dec-1-yl, N-(3-pyridinylmethyl), and N-[[2-(dimethylamino) phenyl]methyl]-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolin-4-amines, as well as N-(1,3-dimethyl-1H-pyrazolo[3,4-b]quinolin-4-yl)-N'-tricyclo[3.3.1.1.su p.3.7 ]dec-1-yl-1,3-propane diamine which were found to be inactive in the interferon assay. Similar derivatives are disclosed in U.S. Pat. No. 4,013,665, issued March 22, 1977.
Stein et al., J. Med. Chem. 1970, 13 (1), 153-155, disclose a series 4-lower-alkylamino and 4-phenylamino-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolines which were tested and found to exhibit no appreciable antimalarial activity.
Zikan et al., Chemical Abstracts 108:204613K, disclose 4-carboxyalkylamino-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolines which are said to be useful as antiviral agents.
Zikan et al. Chemical Abstracts 106:138447q disclose a series of substituted 4-anilino-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolines which are said to be useful as antiviral agents.
Radl et al., Chemical Abstracts 106:18429P, disclose a series of 1-substituted-4-(N-substituted amino)-3-methyl-1H-pyrazolo[3, 4-b]quinolines which are said to be useful as potential antiviral agents. Specifically disclosed are N-[(4-methoxyphenyl) methyl], N-(phenylmethyl), N-(2-phenylethyl) and N-cyclohexyl-1,3-dimethyl- 1H-pyrazolo[3,4-b]quinolin- 4-amines. Radl et al., Chemical Abstracts 105:226434T, disclose a series of 4-hydroxyanilino and 4-alkoxyanilino-1,3-dimethyl-1-H-pyrazolo[3,4-b]quinolines which are said to be useful as potential antiviral agents.